Acetaldehyde → (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine

HRID 429814Notes

Reaction equation

HRID 429814 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].Cl.[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH2:25][C@@H:26]([NH:28][C@H:29]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH3:30])[CH3:27])=[CH:24][C:19]=2[CH2:18][CH2:17]1.C(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C.C(N(CC)CC)C>[O:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH2:25][C@@H:26]([N:28]([C@H:29]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH3:30])[CH2:1][CH3:2])[CH3:27])=[CH:24][C:19]=2[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 177AcetaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 69141969(S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-1-phenylethylamine hydrochloride

Product 1

HCID 57246230(S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amineYield 92.9%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8471TriethylamineSolvent

Procedure

Sodium triacetoxyborohydride (26 grams, 0.123 mole) was added to a suspension of (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-1-phenylethylamine hydrochloride (26 grams, 0.08 mole) in dichloroethane (300 ml) and triethylamine (11.5 ml). After stirring for 5 minutes, acetaldehyde (4.8 ml, 0.086 mole) was added and the mixture was stirred for another 2 hours. Aqueous 5% sodium carbonate (400 ml) was added and the mixture was extracted with methylene chloride. Evaporation of the solvent gave (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine as an oil (23 grams, 91%), M+ 309.

Workup

  1. stirringthe mixture was stirred for another 2 hours
  2. extractionthe mixture was extracted with methylene chloride
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4dd0a8f435a64a02a0a36182c6c64ca1
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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