Chloroacetaldehyde → HCID 59150497, compound

HRID 1668571Notes

Reaction equation

HRID 1668571 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:14]([N:15]=1)=[CH:13][C:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=1[CH:5]=2.[Cl:16][CH2:17][CH:18]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>COCCOC>[Cl:16][CH2:17][CH2:18][N:10]1[CH2:9][CH2:8][C:7]2[CH:13]=[C:14]3[N:15]=[C:2]([CH3:1])[O:3][C:4]3=[CH:5][C:6]=2[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 591504802-Methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine

Product 1

HCID 59150497HCID 59150497, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture 2-methyl-6,7,8,9-tetrahydro-5H-[1,3]oxazolo[4,5-h][3]benzazepine (1 mmol), chloroacetaldehyde (2 mmol), NaBH(OAc)3 (2 mmol) in dry DME (10 ml) was stirred at room temperature for 3 h. The mixture was partitioned between aqueous Na2CO3 (0.5 M) and DCM. The organic layer was collected and the aqueous phase extracted twice with DCM. The combined DCM layers were concentrated and submitted to column chromatography (EtOAc—acetone gradient) to provide the title compound (36% yield).

Workup

  1. customThe mixture was partitioned between aqueous Na2CO3 (0.5 M) and DCM
  2. customThe organic layer was collected
  3. extractionthe aqueous phase extracted twice with DCM
  4. concentrationThe combined DCM layers were concentrated

Sources & evidence

ORD record
ord-752220f6d3f94ed3ba7be2505ff68da7
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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