Benzaldehyde → HCID 178454034, compound

HRID 2268417Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH2:16]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 178419079HCID 178419079, compound

Product 1

HCID 178454034HCID 178454034, compoundYield 51%

Procedure

The title compound was prepared by a similar method to example 5 from tert-butyl trans-4-aminocyclohexylcarbamate (1.0 g, 4.7 mmol) (J. Org. Chem. 8811, 61, 1996), benzaldehyde (530 mg, 5 mmol) and sodium triacetoxyborohydride (2.0 g, 9.4 mmol). The product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (0.73 g) as a solid.

Workup

customThe product was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5)

Sources & evidence

ORD record: ord-295dcfc0c52c4104ba06db1c6039f64c
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326359B1

Reaction notes

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