Formaldehyde → HCID 86640761, compound

HRID 1965936Notes

Reaction equation

HRID 1965936 reaction equation
[NH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C=O.[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>O.CCOC(C)=O>[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].[NH:1]1[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 712Formaldehyde2×HCID 66111Trimethylsilylacetylene2×HCID 92911Decahydroquinoline

Product 1

HCID 86640761HCID 86640761, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of the cis/trans mixture of decahydroquinoline diastereomers (1.20 g, 3.48 mmol), formaldehyde (1.1 mL, 13.9 mmol) as a 37 wt % solution in H2O, trimethylsilyl acetylene (963 μL, 6.95 mmol), and AuBr3 (455 mg, 1.04 mmol) in H2O (2.0 mL) was heated at 75° C. overnight. LC/MS of an aliquot showed the reaction had not gone to completion. The reaction mixture was charged with a second portion of formaldehyde (1.1 mL, 13.9 mmol) as a 37 wt % solution in H2O and trimethylsilyl acetylene (963 μL, 6.95 mmol) and heated at 75° C. for an additional 72 hr. The reaction mixture was diluted with EtOAc and filtered through a Celite pad, washing with EtOAc (25 mL). The solution was concentrated and purified by chromatography, eluting with 0-20% EtOAc/hexanes to give 413 mg (26%) of the cis-decahydroquinoline trimethylsilyl acetylene as a colorless oil confirmed by MS (ESI+): cal'd [M+H]+ 466.6, exp. 466.1.

Workup

  1. filtrationfiltered through a Celite pad
  2. washwashing with EtOAc (25 mL)
  3. concentrationThe solution was concentrated
  4. custompurified by chromatography
  5. washeluting with 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-315097b220134ac58084cf56f98b6c16
Source dataset
uspto-grants-2013_04
Patent number
US08420622B2

Reaction notes

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