4-Methylmorpholine → (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

HRID 339480

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HRID 339480 반응식
[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>COCCOC>[CH2:1]([O:8][CH2:9][C@H:10]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:20])([CH3:19])[CH3:21])[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 4311764Sodium borohydride

생성물 1

HCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol수율 92%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
-20 °C

실험 절차

(2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]propanoic acid (7.2 g, 24.4 mmole) was dissolved in ethylene glycol dimethyl ether (50 mL). N-Methylmorpholine (2.7 ml, 24.4 mmole) was added, and the resulting clear solution was cooled to −20° C. Isobutyl chloroformate (3.19 ml, 24.4 mmole) was added dropwise to cause N-methylmorpholine HCl salt precipitation. Stirring was continued for 15 min and the supernatant was then transferred via a filter-tipped funnel into a rapidly stirred solution of NaBH4 (2.93 g, 73.2 mmole) in ice water and washed with dry DME. After the mixture was stirred for 30 min, it was extracted with EtOAc and washed with H2O. The organic layers were combined, dried over Na2SO4, and concentrated in vacuo. Purification by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.2) afforded tert-butyl N-[(1R)-2-(benzyloxy)-1-(hydroxymethyl)ethyl]carbamate as a white solid (6.3 g, 92%).

후처리

  1. customN-methylmorpholine HCl salt precipitation
  2. washwashed with dry DME
  3. stirringAfter the mixture was stirred for 30 min
  4. extractionit was extracted with EtOAc
  5. washwashed with H2O
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography (silica, 4/1: Hexane/EtOAc, Rf=0.2)

출처 및 근거

ORD 기록
ord-d14da13e9cb94b56a27abd58aeadfe2b
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895497B2

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