Acetic Acid → HCID 69811555, compound

HRID 2190041Notes

Reaction equation

HRID 2190041 reaction equation
[CH2:1]([CH:8]1[CH2:13][C:12]2([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[N:15]=[CH:14]2)[CH2:11][CH2:10][N:9]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH2:1]([CH:8]1[CH2:13][C:12]2([C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[NH:15][CH2:14]2)[CH2:11][CH2:10][N:9]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 68761279HCID 68761279, compound

Product 1

HCID 69811555HCID 69811555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 2′-benzyl-5-chlorospiro[indole-3,4′-piperidine]-1′-carboxylate (200 mg, 0.49 mmol) was dissolved in dichloromethane (5 mL) and then sodium triacetoxy borohydride (206 mg, 0.97 mmol) was added followed by acetic acid (0.5 mL). The resulting mixture was stirred for 2 h at ambient temperature at which time it was quenched by the addition of saturated sodium bicarbonate solution. The mixture was diluted with EtOAc and then washed twice with water and once with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated to give tert-butyl 2′-benzyl-5-chlorospiro[indoline-3,4′-piperidine]-1′-carboxylate. The material thus obtained was used without further purification (185 mg, 92%). LCMS (APCI+) m/z 311.1; Rt=4.32 min.

Workup

  1. customwas quenched by the addition of saturated sodium bicarbonate solution
  2. additionThe mixture was diluted with EtOAc
  3. washwashed twice with water and once with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bdb2332b1ddf4f16bc512ed6ebd26cf9
Source dataset
uspto-grants-2012_12
Patent number
US08324221B2

Reaction notes

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