Bromomethylcyclopropane → 1-Cyclopropylmethylcyclopropylsulfonylamine tert-butylcarbamate

HRID 1815700Notes

Reaction equation

[C:1]([NH:5][C:6](=[O:8])[OH:7])([CH3:4])([CH3:3])[CH3:2].CO[CH2:11][C:12]1([S:15]([NH2:18])(=[O:17])=[O:16])[CH2:14][CH2:13]1.[CH:19]1(CBr)[CH2:21][CH2:20]1>>[C:1]([NH:5][C:6](=[O:7])[OH:8])([CH3:4])([CH3:3])[CH3:2].[CH:19]1([CH2:11][C:12]2([S:15]([NH2:18])(=[O:17])=[O:16])[CH2:14][CH2:13]2)[CH2:21][CH2:20]1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 667523821-Methoxymethylcyclopropylsulfonylamine tert-butylcarbamate

Product 1

HCID 224993121-Cyclopropylmethylcyclopropylsulfonylamine tert-butylcarbamate

Procedure

Step 16IId) This compound, 1-cyclopropyl-methylcyclopropylsulfonylamine tert-butylcarbamate, was obtained in 92% yield according to the procedure described in the synthesis of 1-methoxymethylcyclo-propylsulfonylamine tert-butylcarbamate (Step 15IId) except 1.10 equivalents of cyclopropylmethyl bromide were used as electrophile. The compound was taken directly into the next reaction without purification: 1H NMR (CDCl3) δ 0.10 (m, 2H), 0.51 (m, 2H), 0.67 (m, 1H), 1.10 (m, 2H), 1.49 (s, 9H), 1.62 (m, 2H), 1.87 (d, J=7.0 Hz, 2H).

Workup

customThe compound was taken directly into the next reaction without purification

Sources & evidence

ORD record: ord-47e2b71cf44b47daa93fcb545aced34e
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06878722B2

Reaction notes

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