p-Toluenesulfonic acid → tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate

HRID 451813노트

반응식

HRID 451813 반응식
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH2:14][C@H:15]2[CH2:20][CH2:19][C:18](=[O:21])[N:17]([CH3:22])[CH2:16]2)[CH2:4][O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CO>[OH:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[CH2:14][C@H:15]1[CH2:20][CH2:19][C:18](=[O:21])[N:17]([CH3:22])[CH2:16]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 90495Di-tert-butyl dicarbonateHCID 59201489(S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate

생성물 1

HCID 59201482tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate (230 mg, 0.70 mmol) in MeOH (10 mL) was added p-TSA (30 mg, 0.17 mmol) and stirred at rt overnight. TEA (1 mL) was added, followed by Boc2O (30 mg). The reaction mixture was stirred for another 30 min. The solvent was removed under vacuum to give crude product tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate, which was used for next step without further purification. MS ESI +ve m/z 287 (M+H).

후처리

  1. stirringThe reaction mixture was stirred for another 30 min
  2. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-7a1f4d0b0f414a408a58104c0536043a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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