Diisopropylethylamine → HCID 67606185, compound

HRID 538397Notes

Reaction equation

[NH2:1][CH:2]1[CH:7]2[CH:3]1[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6]2.[OH:15][CH2:16][C:17]1[O:21][N:20]=[C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=1.C(N(CC)C(C)C)(C)C.Cl[C:37](OC1C=CC([N+]([O-])=O)=CC=1)=[O:38]>>[CH2:25]([O:24][C:22]([C:19]1[CH:18]=[C:17]([CH2:16][O:15][C:37]([NH:1][CH:2]2[CH:7]3[CH:3]2[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6]3)=[O:38])[O:21][N:20]=1)=[O:23])[CH3:26]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 821294-Nitrophenyl chloroformate

HCID 8027233Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

HCID 16228674tert-Butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 67606185HCID 67606185, compoundYield 75%

Procedure

The procedure described in Example 3, step 3.4. is followed. Starting from 3.00 g (15.13 mmol) of tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate, 2.58 g (15.13 mmol) of ethyl 5-hydroxymethyl-isoxazole-3-carboxylate, 5.27 ml (30.26 mmol) of N,N-diisopropylethylamine and 3.05 g (15.13 mmol) of para-nitrophenyl chloroformate, 4.50 g of product are obtained in the form of a colourless oil (75%).

Sources & evidence

ORD record: ord-d26d947d94274b559111b4ce660c0812
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865738B2

Reaction notes

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