Reaction #619182

ord-7e60a35bb7a94479a42ae24f39ba8dad

Reaction equation

O=Cc1cnc(NC(=O)N(C2CCCCC2)C2CCCCC2)s1
1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea
[BH4-].[Li+]
lithium borohydride
O=C(Nc1ncc(CO)s1)N(C1CCCCC1)C1CCCCC1
desired compound
Yield 97.0%
O=C(Nc1ncc(CO)s1)N(C1CCCCC1)C1CCCCC1
1,1-Dicyclohexyl-3-(5-hydroxymethyl-thiazol-2-yl)-urea
Yield 97.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherPrepared
  2. 2
    OtherPurification without work-up (silica gel, 10% EtOAc and 2% MeOH in CH2Cl2)

Procedure

Prepared using 1,1-dicyclohexyl-3-(5-formyl-thiazol-2-yl)-urea (50 mg, 0.15 mmol) and lithium borohydride (95 μL, 2M in THF) in MeOH (1 mL). Purification without work-up (silica gel, 10% EtOAc and 2% MeOH in CH2Cl2) afforded 49 mg (97%) of the desired compound.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE045183E1uspto-grants-2014_10