Ethyl bromoacetate → (2S)-1-[N-benzyl-(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol

HRID 1936964Notes

Reaction equation

HRID 1936964 reaction equation
[H-].[Na+].[CH2:3]([N:10]([CH:22]1[CH2:28][CH2:27][CH2:26][C:25]2[C:29]([OH:33])=[CH:30][CH:31]=[CH:32][C:24]=2[CH2:23]1)[CH2:11][C@H:12]([OH:21])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37]>CN(C)C=O.O>[CH2:3]([N:10]([CH:22]1[CH2:28][CH2:27][CH2:26][C:25]2[C:29]([O:33][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:30][CH:31]=[CH:32][C:24]=2[CH2:23]1)[CH2:11][C@H:12]([OH:21])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 70132831(2S)-1-[N-benzyl-(6,7,8,9-tetrahydro-1-hydroxy-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol

Product 1

HCID 9892318(2S)-1-[N-benzyl-(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanolYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

A suspension of 60% sodium hydride (54 mg, washed with n-hexane) in N,N-dimethylformamide (1 ml) was added slowly to a stirred solution of (2S)-1-[N-benzyl-(6,7,8,9-tetrahydro-1-hydroxy-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (512 mg) in N,N-dimethylformamide (5 ml) under ice cooling and the resulting mixture was stirred at the same temperature for 30 minutes. A solution of ethyl bromoacetate (225 mg) in N,N-dimethylformamide (1 ml) was added dropwise therein at the same temperature and the mixture was stirred at the same temperature for 4 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed twice with brine, dried over magnesium sulfate, and evaporated in vacuo to afford (2S)-1-[N-benzyl-(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (0.59 g) as a crude oil.

Workup

  1. stirringat the same temperature and the mixture was stirred at the same temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed twice with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-97d17113573a48f295d212d22211d5ad
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

Loading…