HCID 69904401, compound → HCID 9862003, compound

HRID 850003Notes

Reaction equation

HRID 850003 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH:20]3[CH2:21][CH2:22][CH:23]([CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:19]3[CH2:18][CH2:17][O:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:24]([CH:23]1[N:19]2[CH:20]([CH:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[O:16][CH2:17][CH2:18]2)[CH2:21][CH2:22]1)[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 69904401HCID 69904401, compound

Product 1

HCID 9862003HCID 9862003, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

(1RS,6SR,8aRS)-1-(4-Benzyloxy-phenyl)-6-phenethyl-hexahydro-pyrrolo[2, 1-c][1,4]oxazine (0.09 g, 0.22 mmol) was dissolved in MeOH (5 ml) and hydrogenated in the presence of Pd on C at room temperature and at atmospheric pressure for 4 hours. After filtration and evaporation of the solvent the residue was chromatographed over silica gel (CH2Cl2 --MeOH 19:1) to provide (1RS,6SR,8aRS)-4-(6-phenethyl-hexahydro-pyrrolo[2,1-c][1, 4]oxazin-1-yl)-phenol (25 mg, 35%) as a pink solid, m.p. 170-172° C. MS: m/e=324.3 (M+H+).

Workup

  1. filtrationAfter filtration and evaporation of the solvent the residue
  2. customwas chromatographed over silica gel (CH2Cl2 --MeOH 19:1)

Sources & evidence

ORD record
ord-56022b844c0841c79d1de49d3602ca61
Source dataset
uspto-grants-2000_01
Patent number
US06015824

Reaction notes

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