Benzylamine → HCID 59130267, compound

HRID 1992267Notes

Reaction equation

[CH:1]12[O:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].O=[O+][O-].[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH3-]C#N.[Na+]>CO.C(Cl)Cl.CO>[C:20]1([CH2:19][N:26]2[CH2:6][CH:1]3[O:7][CH:4]([CH2:3][CH:2]3[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:5]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution 1,1-dimethylethyl 7-oxabicyclo[2.2.1]hept-5-en-2-ylcarbamate (1.0 g, 4.74 mmol) in MeOH/DCM (48 mL, 1:1) at −78° C. was bubbled through O3 until the solution maintained a blue color. N2 was then bubbled through until the blue color dissipated and a solution of benzylamine (0.49 mL, 4.5 mmol) and NaBH3CN (1.19 g, 19.0 mmol) in MeOH (22 mL) was added dropwise. After gradually warming to 25° C. over 12 hr, the mixture was partitioned between 6N NaOH and DCM. The aqueous layer was back-extracted several times with DCM and the combined organic fractions were concentrated and purified by column chromatography (silica, 0-1% MeOH in DCM (1% NH4OH )) affording the title compound as a clear oil (560 mg, 37%): LC/MS (ES) m/e 319 (M+H)+.

Workup

temperaturemaintained a blue color
customN2 was then bubbled through until the blue color
customthe mixture was partitioned between 6N NaOH and DCM
extractionThe aqueous layer was back-extracted several times with DCM
concentrationthe combined organic fractions were concentrated
custompurified by column chromatography (silica, 0-1% MeOH in DCM (1% NH4OH ))

Sources & evidence

ORD record: ord-c3b8e875a5904f4d9bc8b596729b37b8
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648980B2

Reaction notes

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