1,1-dimethylethyl 9-[(phenylmethyl)oxy]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate → tert-butyl 9-hydroxy-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

HRID 1514223Notes

Reaction equation

HRID 1514223 reaction equation
C1(C[O:8][C:9]2[C:19]3[O:18][CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[C:19]2[O:18][CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 594034471,1-dimethylethyl 9-[(phenylmethyl)oxy]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Product 1

HCID 59403444tert-butyl 9-hydroxy-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1,1-dimethylethyl 9-[(phenylmethyl)oxy]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 61) (8.25 g, 23.21 mmol) in ethanol (100 ml) was hydrogenated with 10% palladium on carbon (0.825 g, 7.75 mmol) for 18 hours, filtered and evaporated to give 6.16 g of white solid. MS (ES−): C21H25NO4 requires 265; found 264 [M−H+].

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-0972fe45d0d440349bc00b18fda8efff
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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