Acetaldehyde → HCID 67772427, compound

HRID 1808793Notes

Reaction equation

HRID 1808793 reaction equation
[N:1]1([CH2:5][C@@H:6]([NH2:10])[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1.[CH:11](=O)[CH3:12].[Na].O>C(Cl)Cl>[N:1]1([CH2:5][C@@H:6]([NH:10][CH2:11][CH3:12])[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 962WaterHCID 5360545SodiumHCID 67775438HCID 67775438, compound2×

Product 1

HCID 67772427HCID 67772427, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1-(Azetidin-1-yl)-3-methylbutan-2-amine (Compound U) (0.420 g, 2.95 mmol) and acetaldehyde (0.166 mL, 2.95 mmol) was mixed in DCM (10 mL). Sodium triacetoxyhydroborate (0.813 g, 3.84 mmol) was added in small portions and the resultant mixture was stirred at rt for 5 h. Water was added and the pH was adjusted to pH9. The water phase was extracted with DCM (4×50 mL). The combined organic layers were combined and washed with brine, passed through phase separator and evaporated under reduced pressure to give the title compound (0.1 g, 20%). The obtained crude product was used without further purification. LCMS (M+H)+: 171.

Workup

  1. extractionThe water phase was extracted with DCM (4×50 mL)
  2. washwashed with brine
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-15a9d092df0d4cbab157b9285eeb1635
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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