Reaktion #557845

ord-af662f47bb524c0c88ee85523a849c1d

Reaktionsgleichung

CC1(C)CCC2(CC1)N1[C@H](c3ccccc3)[C@H](c3ccccc3)OC(=O)[C@H]1[C@H](c1cccc(Cl)c1F)[C@@]21C(=O)Nc2nc(Cl)ccc21
compound
CC1(C)CCC2(CC1)N1[C@H](c3ccccc3)[C@H](c3ccccc3)OC(=O)[C@H]1[C@H](c1cccc(Cl)c1F)[C@@]21C(=O)Nc2nc(Cl)ccc21
(3′S,4′R,7′S,8′S,8a′R)-6″-chloro-8′-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3′,4′-diphenyl-3′,4′,8′,8a′-tetrahydro-1′H-dispiro[cyclohexane-1,6′-pyrrolo[2,1-c][1,4]oxazine-7′,3″-pyrrolo[2,3-b]pyridine]-1′,2″(1″H)-dione
N[C@H]1CC[C@H](CO)CC1
(trans-4-aminocyclohexyl)methanol
→
CC1(C)CCC2(CC1)N([C@H](c1ccccc1)[C@@H](O)c1ccccc1)[C@@H](C(=O)N[C@H]1CC[C@H](CO)CC1)[C@H](c1cccc(Cl)c1F)C21C(=O)Nc2nc(Cl)ccc21
title compound
Ausbeute 83.4%
CC1(C)CCC2(CC1)N([C@H](c1ccccc1)[C@@H](O)c1ccccc1)[C@@H](C(=O)N[C@H]1CC[C@H](CO)CC1)[C@H](c1cccc(Cl)c1F)C21C(=O)Nc2nc(Cl)ccc21
(4′S,5′R)-6″-chloro-4′-(3-chloro-2-fluorophenyl)-1′-[(1R,2S)-2-hydroxy-1,2-diphenylethyl]-N-[trans-4-(hydroxymethyl)cyclohexyl]-4,4-dimethyl-2″-oxo-1″,2″-dihydrodispiro[cyclohexane-1,2′-pyrrolidine-3′,3″-pyrrolo[2,3-b]pyridine]-5′-carboxamide
Ausbeute 83.4%

Edukte

CC1(C)CCC2(CC1)N1[C@H](c3ccccc3)[C@H](c3ccccc3)OC(=O)[C@H]1[C@H](c1cccc(Cl)c1F)[C@@]21C(=O)Nc2nc(Cl)ccc21
compound
CC1(C)CCC2(CC1)N1[C@H](c3ccccc3)[C@H](c3ccccc3)OC(=O)[C@H]1[C@H](c1cccc(Cl)c1F)[C@@]21C(=O)Nc2nc(Cl)ccc21
(3′S,4′R,7′S,8′S,8a′R)-6″-chloro-8′-(3-chloro-2-fluorophenyl)-4,4-dimethyl-3′,4′-diphenyl-3′,4′,8′,8a′-tetrahydro-1′H-dispiro[cyclohexane-1,6′-pyrrolo[2,1-c][1,4]oxazine-7′,3″-pyrrolo[2,3-b]pyridine]-1′,2″(1″H)-dione
N[C@H]1CC[C@H](CO)CC1
(trans-4-aminocyclohexyl)methanol

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONtreated in the same way as in Step 2 of Example 1

Vorschrift

The compound (260 mg, 0.39 mmol) obtained in Step 1 above and (trans-4-aminocyclohexyl)methanol (100 mg, 0.77 mmol) were used as starting materials and treated in the same way as in Step 2 of Example 1 to give 260 mg (83%) of the title compound as a pale yellow oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08629133B2uspto-grants-2014_01