Ethylamine → HCID 68616941, compound

HRID 1158377Notes

Reaction equation

HRID 1158377 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH:34]=O)[CH2:9]1)=O)(C)(C)C.[CH2:36]([NH2:38])[CH3:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:36]([NH:38][CH2:34][C@@H:10]1[CH2:9][NH:8][CH2:12][C@H:11]1[CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=1)[CH3:37]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59512275(3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68616941HCID 68616941, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The corresponding enantiomer N-((3S,4R)-4-Ethylaminomethyl-pyrrolidin-3-ylmethyl)-N-isopropyl-4-methoxy-3-(3-methoxy-propoxy)-benzamide is obtained as follows: A solution of (3S,4R)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.27 g, 2.58 mmol) and gaseous ethylamine (0.704 g, 15.5 mmol; Fluka 02940) in 1,2-dichloroethane (10 mL) is stirred at room temperature for 30 min, then sodium triacetoxyborohydride (1.37 g, 6.45 mmol) is added in one portion and the mixture is stirred overnight. The organic phase is washed with saturated aqueous NaHCO3 solution, the water layers are re-extracted with CH2Cl2, and the combined organics are dried (Na2SO4) and evaporated to dryness to give the title compound. MS: 522.2 [M+H]+.

Workup

  1. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  2. extractionthe water layers are re-extracted with CH2Cl2
  3. dry with materialthe combined organics are dried (Na2SO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-cc6ba09f03264f14a8caea61855b0449
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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