3-Thiophenecarboxaldehyde → HCID 63248157, compound

HRID 1711161Notes

Reaction equation

HRID 1711161 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:15]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:20][C:17]2[CH:18]=[CH:19][S:15][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 681353-ThiophenecarboxaldehydeHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 63248157HCID 63248157, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Using general procedure A, 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.800 g, 4.30 mmol), thiophene-3-carbaldehyde (0.480 g, 4.30 mmol), acetic acid (20 drops, cat.) and sodium triacetoxyborohydride (1.27 g, 6.02 mmol) were combined in 1,2-dichloroethane (40 ml) and the resulting mixture was stirred at rt for 16 h. Standard basic workup gave the crude product as a tan oil. Purification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v) gave 4-[(thiophen-3-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester as a pale yellow oil (0.886 g, 73%). 1H-NMR (CDCl3) δ 1.27 (m, 3H), 1.45 (s+m, 1H), 1.84 (d, 2H, J=12.0 Hz), 2.66 (m, 1H), 2.80 (t, 2H, J=12.0 Hz), 3.85 (s, 2H), 4.01 (br d, 2H), 7.03 (d, 1H, J=6.0 Hz), 7.12 (s, 1H), 7.29 (m, 1H).

Workup

  1. customStandard basic workup gave the crude product as a tan oil
  2. customPurification by column chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 96:3:1, v/v/v)

Sources & evidence

ORD record
ord-0c3ee6803ab4469481568e982a3e4820
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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