Water → ((3S,6R)-6-hydroxy-1-methyl-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester

HRID 2224025Notes

Reaction equation

HRID 2224025 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([O:15][Si](C(C)(C)C)(C)C)[CH2:11][N:10]([CH3:23])[C:9]1=[O:24])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]1[CH2:14][CH2:13][C@@H:12]([OH:15])[CH2:11][N:10]([CH3:23])[C:9]1=[O:24])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69266856[(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 69268961((3S,6R)-6-hydroxy-1-methyl-2-oxo-azepan-3-yl)-carbamic acid tert-butyl esterYield 96.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [(3S,6R)-6-(tert-butyl-dimethyl-silanyloxy)-1-methyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.85 g, 2.27 mmol) in THF (40 mL) is added tetrabutylammonium fluoride (3 mL 1M THF, 3 mmol) at room temperature. The reaction solution is stirred for 4 h, then H2O (40 mL) is added and the solution concentrated under vacuum to ½ its volume and extracted 3× with CH2Cl2 (40 mL). The combined CH2Cl2 extracts are adsorbed on silica and chromatographed (5% CH3OH/CH2Cl2) to give 0.568 g (72%) of ((3S,6R)-6-hydroxy-1-methyl-2-oxo-azepan-3-yl)-carbamic acid tert-butyl ester as a white solid. 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.7-2.05 (m, 4H), 3.1 (s, 3H), 3.37 (dd, 1H), 3.73 (d, 1H), 4.07 (m, 1H), 4.31 (m, 1H), 6.0 (d, 1H).

Workup

  1. concentrationthe solution concentrated under vacuum
  2. extractionextracted 3× with CH2Cl2 (40 mL)
  3. customchromatographed (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-1e0c73c7c85949d3a2153bf08db232ec
Source dataset
uspto-grants-2008_05
Patent number
US07378410B2

Reaction notes

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