Sodium sulfate decahydrate → tert-butyl N-(1-(hydroxymethyl)cyclobutyl)carbamate

HRID 246283Notes

Reaction equation

C([O:3][C:4]([C:6]1([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[C:14]([O:13][C:11](=[O:12])[NH:10][C:6]1([CH2:4][OH:3])[CH2:9][CH2:8][CH2:7]1)([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 15 ml round-bottomed flask, 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid ethyl ester (180 mg, 0.74 mmol) was dissolved in THF (4 ml). The colorless solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.78 ml, 0.78 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution has ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give (1-hydroxymethyl-cyclobutyl)-carbamic acid tert-butyl ester as an off-white waxy solid which was used without further purification.

Workup

customthe ice bath was removed
additionsodium sulfate was added
stirringthe mixture was stirred for 30 min at room temperature
filtrationThe suspension was filtered over Celite
washrinsed with ethyl acetate/methanol
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-9a12f6eb8c9248789c82b99d7f21188b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658646B2

Reaction notes

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