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Water → rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

HRID 81349
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HRID 81349 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@@H:10]1[OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:28]OS(OC)(=O)=O.O>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@H:10]1[O:25][CH3:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

7

반응물 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 58303445Phenylmethyl (3S,4S)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-1-piperidinecarboxylate

생성물 1

HCID 58522570rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

시약·촉매·용매 2

HCID 66133
Benzyl triethylammonium chloride
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

benzyl (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-piperidine-1-carboxylate (5.00 g) is dissolved in THF (6 mL) and combined with 30 mL aqueous, semiconcentrated NaOH solution, benzyltriethylammonium chloride as well as dimethylsulphate (2.26 mL). After 22 h H2O (200 mL) is added and the mixture is extracted with EtOAc (150 mL). The organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. Purification is carried out using a silica gel column (cHex/EtOAc 65/35).

후처리

  1. extractionthe mixture is extracted with EtOAc (150 mL)
  2. customThe organic phase is dried on magnesium sulphate
  3. filtrationfiltered off from the desiccant and the solvent
  4. customPurification

출처 및 근거

ORD 기록
ord-4ced7a16961f4e099f0f5614f0aa8edc
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846689B2

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