Cyclopropylamine → HCID 45087015, compound

HRID 859876Notes

Reaction equation

HRID 859876 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([C:14]([OH:16])=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(N=C=NCCCN(C)C)C.Cl>ClCCl>[CH2:1]([N:8]1[CH2:12][C@H:11]([CH3:13])[C@@H:10]([C:14]([NH:20][CH:17]2[CH2:19][CH2:18]2)=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 69828CyclopropylamineHCID 1515523604798-82-5HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 45087015HCID 45087015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3R,4R)-1-Benzyl-4-methyl-3-pyrrolidinecarboxylic acid (6.27 g) was suspended in dichloromethane (250 mL). To this suspension, cyclopropylamine (1.76 mL) and hydrochloric acid 1-ethyl-(3-dimethylaminopropyl)carbodiimide (12.2 g) were sequentially added and the mixture was stirred at room temperature for 4 hours. Subsequently, the reaction mixture was washed with water, was dried over anhydrous sodium sulfate, and was then concentrated under reduced pressure. The resulting residue was purified on a silica gel column (ethyl acetate: methanol=10:1) to give 3.32 g of (3R,4R)-1-benzyl-N-cyclopropyl-4-methyl-3-pyrrolidinecarboxamide as a white crystal.

Workup

  1. washSubsequently, the reaction mixture was washed with water
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated under reduced pressure
  4. customThe resulting residue was purified on a silica gel column (ethyl acetate: methanol=10:1)

Sources & evidence

ORD record
ord-7c2e2d0048fd4424b6c5c657a59f4b0c
Source dataset
uspto-grants-2006_12
Patent number
US07153851B2

Reaction notes

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