Acetaldehyde, 2,2-dimethoxy- → HCID 66782864, compound

HRID 1096281Notes

Reaction equation

HRID 1096281 reaction equation
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C@@H:7]1[CH2:14][N:13]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:12][CH2:11][C:8]21[CH2:10][CH2:9]2)([CH3:4])([CH3:3])[CH3:2].[CH3:21][O:22][CH:23]([O:26][CH3:27])[CH:24]=O.[BH4-].[Na+]>CO>[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C@@H:7]1[CH2:14][N:13]([CH2:15][CH2:16][CH2:17][NH:18][CH2:24][CH:23]([O:26][CH3:27])[O:22][CH3:21])[CH2:12][CH2:11][C:8]21[CH2:10][CH2:9]2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 4311764Sodium borohydrideHCID 66783237HCID 66783237, compound

Product 1

HCID 66782864HCID 66782864, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propylamine (234 mg, 0.78 mmol) and dimethoxyacetaldehyde (45% solution in TBME, 0.20 mL, 0.78 mmol) in MeOH (3 mL) was stirred for 5 h at RT, then sodium borohydride (47 mg, 1.25 mmol) was added, then after 15 min the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc) afforded the title compound (210 mg, 69%). Light yellow gum, MS: 387.4 (M+H)+.

Workup

  1. customafter 15 min the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-bf41a908ecfc454d9a2702ae76d06b25
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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