Bicyclo(3.1.1)heptane-3-methanamine, 2,6,6-trimethyl- → alpha-Isocyanopropionic acid (+)-3-pinylmethylamide

HRID 1278093Notes

Reaction equation

HRID 1278093 reaction equation
[N+:1]([CH:3]([CH3:8])[C:4](OC)=[O:5])#[C-:2].[NH2:9][CH2:10][CH:11]1[CH2:16][CH:15]2[CH2:17][CH:13]([C:14]2([CH3:19])[CH3:18])[CH:12]1[CH3:20]>>[CH:13]12[CH2:17][CH:15]([C:14]1([CH3:18])[CH3:19])[CH2:16][CH:11]([CH2:10][NH:9][C:4](=[O:5])[CH:3]([N+:1]#[C-:2])[CH3:8])[CH:12]2[CH3:20]

Participants

3

Reactant 2

HCID 106576Bicyclo(3.1.1)heptane-3-methanamine, 2,6,6-trimethyl-HCID 2734780Methyl 2-isocyanopropanoate

Product 1

HCID 54049847alpha-Isocyanopropionic acid (+)-3-pinylmethylamide

Procedure

A mixture of 5.7 g (50 mmoles) of methyl α-isocyanopropionate and 8.3 g (50 mmoles) of (+)-3-aminomethylpinane is stirred for 15 hours at room temperature, initially with slight cooling. After distilling off the resulting methanol in a high vacuum at 80° C., 11.6 g of crystalline α-isocyanopropionic acid (+)-3-pinylmethylamide of melting point 58°-59° C. remain. IR spectrum (KBr): 3,230 (N--H), 2,130 (N≡C), 1,670 cm-1 (C=O).

Workup

  1. distillationAfter distilling off the resulting methanol in a high vacuum at 80° C.

Sources & evidence

ORD record
ord-b2505be8d0aa47908e619e9bcf429543
Source dataset
uspto-grants-1981_07
Patent number
US04280008

Reaction notes

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