Piperidine → (R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

HRID 1444713Notes

Reaction equation

HRID 1444713 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][CH2:7][CH2:6]2)=O.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[N:21]1([CH2:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][CH2:7][CH2:6]3)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 56594896(R)-tert-butyl 6-formyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Product 1

HCID 56594897(R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 100 mL of 1,2-dichloroethane, 5.0 g (18 mmol) of (R)-tert-butyl 6-formyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate and 3.1 g (36 mmol) of piperidine were combined. Next, 7.6 g (36 mmol) of sodium triacetoxy borohydride was added and the mix was stirred under nitrogen overnight. The mix was then dissolved in 100 mL of ethyl acetate, washed with 25 mL of saturated sodium bicarbonate, washed with 25 mL of brine, dried with sodium sulfate and concentrated to yield the crude material.

Workup

  1. washwashed with 25 mL of saturated sodium bicarbonate
  2. washwashed with 25 mL of brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a4e70acb009447198e41000c62bb26fc
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

Loading…