Benzaldehyde → (S)-tert-Butyl (1-benzylpiperidin-3-yl)carbamate

HRID 1467329Notes

Reaction equation

HRID 1467329 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:2]1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Na]>C(O)(=O)C.ClCCl>[CH2:15]([N:1]1[CH2:6][CH2:5][CH2:4][C@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 5360545Sodium

Product 1

HCID 10541535(S)-tert-Butyl (1-benzylpiperidin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (2 mL) and acetic acid (2 drops) was added to (S)-tert-butyl piperidin-3-ylcarbamate (100 mg, 0.5 mmol) and benzaldehyde (1 mmol). The reaction was stirred for 15 minutes. Sodium triacetoxyborohydride (422 mg, 2 mmol) was added in one portion. The reaction was stirred overnight. Saturated sodium bicarbarbonate (5 mL) was added. The reaction was stirred for an additional 5 minutes and was extracted with dichloromethane (3×10 mL). The extracts were combined, dried with anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was progressed to the next step without purification.

Workup

  1. stirringThe reaction was stirred overnight
  2. stirringThe reaction was stirred for an additional 5 minutes
  3. extractionwas extracted with dichloromethane (3×10 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was progressed to the next step without purification

Sources & evidence

ORD record
ord-e0a6acb367f045fb8c3c66ececf2b489
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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