Sodium borohydride → (+/-)[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)butyl]amine

HRID 20803Notes

Reaction equation

HRID 20803 reaction equation
[CH3:1][C:2]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)([CH2:5][CH3:6])[C:3]#[N:4].[C:12]1([Li])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+].CC(N1CCCC1)(C)C(N)C1C=CC=CC=1>C(OCCCC)CCC.C1COCC1.CO>[CH3:1][C:2]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)([CH2:5][CH3:6])[CH:3]([NH2:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 4311764Sodium borohydride2×HCID 25158607[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)propyl]amineHCID 438028382-Methyl-2-(1-pyrrolidinyl)butanenitrileHCID 178506676HCID 178506676, compound

Product 1

HCID 59347809(+/-)[2-Methyl-1-phenyl-2-(1-pyrrolidinyl)butyl]amineYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Procedure

The title compound (13.4 g, 94%) was prepared from 2-methyl-2-(1-pyrrolidinyl)butanenitrile D21 (9.6 g, 0.063 mol) and phenyllithium in dibutylether (63 ml of a 2M solution; 0.126 mol) in THF (200 ml), followed by reaction with sodium borohydride (3.5 g, 0.092 mol) in methanol (200 ml) in a similar manner to that described in D5, except that after addition of the sodium borohydride stirring was continued with ice cooling for 0.5 hours then at room temperature for 66 hours. Mass spectrum (Electrospray LC/MS), ES+: Found 233 (MH+). C15H24N2 requires 232. Ret. times 0.78 and 1.06 min.

Workup

  1. waitat room temperature for 66 hours
  2. customtimes 0.78 and 1.06 min.

Sources & evidence

ORD record
ord-e0566abf77a540a89a8c485236349865
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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