反応 #582495

反応方程式

Et3N

DMSO

oxalyl chloride

40

(S)-2-(N,N-Dibenzylamino)-1-propanol

→

yellow oil

収率 98.0%

(S)-2-(N,N-Dibenzylamino)propionaldehyde

収率 98.0%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.WAITAfter 30 minutes
2. 2
   抽出The solution was extracted with satd
3. 3
   抽出NaHCO3 (20 mL) and the aqueous layer was extracted with CH2Cl2 (2×15 mL)
4. 4
   洗浄The organic layer was washed with satd
5. 5
   乾燥NaCl solution, dried with MgSO4
6. 6
   濃縮an concentrated in vacuo at rt

実験手順

Dry DMSO (0.53 mL, 7.43 mmol) was added to a stirred solution of oxalyl chloride (0.31 mL, 3.6 mmol) in CH2Cl2 (7.5 mL) at −78° C. The solution was allowed to stir 15 minutes followed by the addition of 40 (740 mg, 2.90 mmol) in CH2Cl2 (7.5 mL). After 30 minutes, Et3N (1.0 mL, 7.2 mmol) was added and allowed to warm to rt. The solution was extracted with satd. NaHCO3 (20 mL) and the aqueous layer was extracted with CH2Cl2 (2×15 mL). The organic layer was washed with satd. NaCl solution, dried with MgSO4 an concentrated in vacuo at rt to give 720 mg (98% yield) of a yellow oil which became a solid when cooled to −20° C. The aldehyde was used without further purification: mp 52-54° C. Lit. mp 55.5° C.; [α]26D=−36.0 (c 1,CHCl3 Lit. [α]20D=−35.1 (c 1, EtOAc); 1H NMR (400 MHz, CDCl3) δ 1.19 (d, 2H, J=7.0 Hz), 3.34 (q, 1H, J=7.0 Hz), 3.58 (d, 2H, J=13.7 Hz), 3.74 (d, 2H, J=13.7 Hz), 7.26 (m, 2H), 7.33 (m, H), 7.42 (m,4H), 9.74 (s, 1H); 13C NMR (100 MHz) δ 6.7, 54.9, 62.8, 3.3, 4.4, 4.8, 139.1, 204.6; FABMS m/z 408.2 (M+MB), 254.2 (M+H), 22.2 (M—CHO); HRFABMS calcd for C17H20NO Mr 254.1545 (M+H), found Mr254.1545. See, Dix et al., Arch Pharm (Weinheim) 1995, 328, 203-205.

出典