(Dimethyl sulfide)trihydroboron → Tert-butyl 3-cyclohexyl-3-(hydroxymethyl)-8-azabicyclo[3.2.1]octane-8-carboxylate

HRID 1178895Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)([C:16](O)=[O:17])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.CSC>O1CCCC1>[CH:19]1([C:11]2([CH2:16][OH:17])[CH2:10][CH:9]3[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-(tert-butoxycarbonyl)-3-cyclohexyl-8-azabicyclo[3.2.1]octane-3-carboxylic acid (3-2) (1.47 g, 4.35 mmol) in 50 mL of anhydrous tetrahydrofuran was added borane-methyl sulfide complex (8.70 mL, 17.4 mmol, 2.0 M in tetrahydrofuran) dropwise at room temperature. The mixture was stirred at 50° C. for 48 hours and the volatiles were removed under vacuum Purification of the crude residue by flash chromatography over silica gel (50% ethyl acetate/hexanes as eluent) afforded (3-3) as a white solid.

Workup

customthe volatiles were removed under vacuum Purification of the crude residue by flash chromatography over silica gel (50% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record: ord-a09b9cb7d05847a78edaaa0a2d23736e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276520B2

Reaction notes

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