4-Amino-1-Boc-piperidine → HCID 58997004, compound

HRID 251169Notes

Reaction equation

HRID 251169 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=O)(C)(C)C.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:25]2[C:26]([CH:31]=O)=[N:27][CH:28]=[CH:29][CH:30]=2)([CH3:24])[CH3:23])=[CH:18][CH:17]=1.[BH-](O[C:43]([CH3:45])=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:18][C:19]1[C:43]([CH2:45][N:14]([CH2:31][C:26]2[C:25]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=3)([CH3:24])[CH3:23])=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:27][CH:26]=[C:25]([CH3:30])[CH:22]=1

Participants

5

Reactant 3

HCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 865947653-[1-(4-Fluoro-phenyl)-1-methyl-ethyl]pyridine-2-carbaldehyde

Product 1

HCID 58997004HCID 58997004, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 4-amino-piperidine-1-carboxylic acid tert-butyl ester in CH2Cl2 with 3-[1-(4-fluoro-phenyl)-1-methyl-ethyl]-pyridine-2-carbaldehyde and NaBH(OAc)3 gave the amine. 1H NMR (CDCl3) δ 1.10 (m, 2H), 1.43 (s+m, 12H), 1.66 (s, 6H), 2.21 (m, 1H), 2.62 (m, 2H), 3.33 (m, 1H), 3.87 (br d, 2H), 6.97 (t, 2H, J=7.5 Hz), 7.11 (dd, 2H, J=9.0, 3.0 Hz), 7.25 (dd, 1H, J=7.5, 3.0 Hz), 7.86 (d, 1H, J=9.0 Hz), 8.46 (d, 1H, J=3.0 Hz).

Sources & evidence

ORD record
ord-51c23c176ce54ab0894b7d8b1ce3eac2
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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