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

HRID 451813ノート

反応式

HRID 451813 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7a1f4d0b0f414a408a58104c0536043a
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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