Sodium Hydroxide → HCID 69904401, compound

HRID 1859027Notes

Reaction equation

HRID 1859027 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), 5 N 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-2c7ec6b9d74c4abe851e2eee0f46b774
Source dataset
uspto-grants-2000_11
Patent number
US06153624

Reaction notes

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