Sodium borohydride → N-(tert-butyl)-1-(hydroxymethyl)cyclopropane-1-sulfonamide

HRID 1852056Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1([CH:12]=[O:13])[CH2:11][CH2:10]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.[Cl-].[Na+].O>[C:1]([NH:5][S:6]([C:9]1([CH2:12][OH:13])[CH2:10][CH2:11]1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A round-bottom flask equipped with a stir bar was charged with a solution of N-(tert-butyl)-1-formylcyclopropane-1-sulfonamide (8.89 g, 43.3 mmol) in MeOH (110 mL). The solution was cooled to 0° C. and to the solution was added portionwise sodium borohydride (1.64 g, 43.3 mmol). The solution was stirred for 1 h. To the solution was added brine and the mixture was stirred for 15 min. The mixture was concentrated in vacuo to remove MeOH and the aqueous solution was then transferred to separatory funnel and was twice extracted with EtOAc. The combined organics were washed with sat. aq. NaCl; dried over MgSO4; filtered; and then concentrated in vacuo to afford N-(tert-butyl)-1-(hydroxymethyl)cyclopropane-1-sulfonamide as a colorless, crystalline solid (8.66 g, 96%). 1H NMR (400 MHz, CDCl3) δ 4.35 (br. s., 1H), 3.86 (d, J=6.0 Hz, 2H), 2.77 (t, J=6.0 Hz, 1H), 1.50-1.45 (m, 2H), 1.39 (s, 9H), 1.06-1.01 (m, 2H).

Workup

customA round-bottom flask equipped with a stir bar
stirringthe mixture was stirred for 15 min
concentrationThe mixture was concentrated in vacuo
customto remove MeOH
customthe aqueous solution was then transferred to separatory funnel
extractionwas twice extracted with EtOAc
washThe combined organics were washed with sat. aq. NaCl
dry with materialdried over MgSO4
filtrationfiltered
concentrationand then concentrated in vacuo

Sources & evidence

ORD record: ord-c55b5ee365264734b22bb5cbe2b50c17
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957203B2

Reaction notes

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