Acetic Acid → Cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-nitro-benzyl)-amine

HRID 78903Notes

Reaction equation

HRID 78903 reaction equation
[CH:1]([C@H:14]1[O:19][CH2:18][C@@H:17]([NH2:20])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)([O-:23])=[O:22].C(O)(=O)C.[BH3-]C#N.[Na+]>ClCCCl.CO>[CH:1]([C@H:14]1[O:19][CH2:18][C@@H:17]([NH:20][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([N+:21]([O-:23])=[O:22])=[CH:25][CH:26]=2)[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5414-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11565229Cis-(6-benzhydryl-tetrahydropyran-3-yl)-amine

Product 1

HCID 11531477Cis-(6-benzhydryl-tetrahydropyran-3-yl)-(4-nitro-benzyl)-amineYield 80%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

Trans-5-amino-2-diphenylmethyl-tetrahydropyran 15 (0.1 g, 0.38 mmol) was reacted with 4-nitrobenzaldehyde (0.057 g, 0.38 mmol) in the presence of glacial acetic acid (0.023 g, 0.38 mmol) in 1,2-dichloroethane (20 ml), and then reduced by NaCNBH3 (0.03 g, 0.45 mmol) in methanol (5 ml) (Procedure D) to give compound 16d (0.12 g, 80%) as an oil.

Sources & evidence

ORD record
ord-412b31af65324cad9a515bb2252d48be
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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