HCID 69904401, compound → HCID 9862003, compound

HRID 1859026Notes

Reaction equation

HRID 1859026 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+). Following the general method of example 35 the compounds of examples 36 to example 38 were prepared.

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-b31a9ea9a0414bac9e415943c65ca8f3
Source dataset
uspto-grants-2000_11
Patent number
US06153624

Reaction notes

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