Piperidine → HCID 18448551, compound

HRID 32065Notes

Reaction equation

HRID 32065 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[C:15]([Si:19]([CH3:34])([CH3:33])[O:20][CH:21]1[C:30]2[C:25](=[C:26]([CH:31]=O)[CH:27]=[CH:28][CH:29]=2)[O:24][CH2:23][CH2:22]1)([CH3:18])([CH3:17])[CH3:16].[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>ClC(Cl)C>[C:15]([Si:19]([CH3:33])([CH3:34])[O:20][CH:21]1[C:30]2[C:25](=[C:26]([CH2:31][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[CH:27]=[CH:28][CH:29]=2)[O:24][CH2:23][CH2:22]1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 184485964-(Tert-butyl-dimethyl-silanyloxy)-chroman-8-carbaldehyde

Product 1

HCID 18448551HCID 18448551, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

NaBH(OAc)3 (3.86 g, 18.21 mmol) was added to a dichloroethane (30 mL) solution of 4-(tert-butyl-dimethyl-silanyloxy)-chroman-8-carbaldehyde (Step B) (2.66 g, 9.10 mmol) and piperidine (2.70 mL, 27.31 mmol) at RT. After stirring for 1 h, the reaction was quenched with MeOH (10 mL) while the stirring was continued for 20 more min. The reaction was diluted with CH2Cl2 (200 mL) and washed with saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo from heptane to provide the title compound.

Workup

  1. customthe reaction was quenched with MeOH (10 mL) while the stirring
  2. additionThe reaction was diluted with CH2Cl2 (200 mL)
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo from heptane

Sources & evidence

ORD record
ord-30a7e26a6ce442dbb1ea1ec9a26d2e79
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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