Sodium Hydroxide → HCID 69904401, compound

HRID 850004Notes

Reaction equation

HRID 850004 reaction equation
[CH2:1]([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[C:18](=O)[CH2:17][O:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][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:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 69903174HCID 69903174, compound

Product 1

HCID 69904401HCID 69904401, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (1RS,6RS,8aSR)-1-(4-Benzyloxy-phenyl)-6-phenethyl-tetrahydro-pyrrolo[2, 1-c][1,4]oxazin-4-one (0.12 g, 0.28 mmol) in THF (1 ml) was added dropwise to a 0° C. suspension of LiAlH4 (0.021 g, 0.56 mmol) in THF (1 ml). Reaction mixture was stirred at room temperature for 2 hours then cooled to 0° C. and treated successively with H2O (25 ml), 5N NaOH (25 ml), H2O (75 ml). Reaction mixture was stirred at room temperature for 30 min. and Na2SO4 was added. After filtration, evaporation of the solvent provided (1RS,6RS,8aSR)-1-(4-benzyloxy-phenyl)-6-phenethyl-hexahydro-pyrrolo[2,1-c][1,4]oxazine (90 mg, 78%) as a colorless oil. MS: m/e=414.5 (M+H+). Following the general method of example 40 the compound of example 41 was prepared.

Workup

  1. customReaction mixture
  2. temperaturethen cooled to 0° C.
  3. customReaction mixture
  4. stirringwas stirred at room temperature for 30 min.
  5. filtrationAfter filtration, evaporation of the solvent

Sources & evidence

ORD record
ord-3418984c79214f34804888e130acb85e
Source dataset
uspto-grants-2000_01
Patent number
US06015824

Reaction notes

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