3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → tert-Butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 366723

반응식

HRID 366723 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]=O)[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]C(C)([O-])C.[K+].C(OP(C=[N+]=[N-])(=O)OCC)C>CCOCC>[C:6]([N:8]1[C@@H:12]([C:13]#[CH:17])[CH2:11][O:10][C:9]1([CH3:16])[CH3:15])([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7]

참가 물질

5

반응물 3

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 10943016Diazomethyl-phosphonic-acid-diethylesterHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11160457tert-Butyl (4S)-4-ethynyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

(S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine was prepared according to Method X above by the treatment of tert-butyl-(R)-4-formyl-2,2-dimethyl-3-oxazolidine-carboxylate (1.00 g, 4.36 mmol) (Aldrich) with potassium tert-butoxide (730 mg, 6.54 mmol) and diazomethyl-phosphonic-acid-diethylester (1.20 g, 6.54 mmol) (Method X above). The reaction was allowed slowly to warm up to room temperature and stirred for a total of 12 hrs. (S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine was obtained after silica gel column chromatography with 20% Et2O in hexanes. (Yield 420 mg, 43%).

후처리

  1. custom(S)-N-Boc-2,2-dimethyl-4-ethynyl-oxazolidine was prepared

출처 및 근거

ORD 기록
ord-ad3086333bef492fb2b5ef584b0234ea
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130239

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