Water → HCID 21476660, compound

HRID 2293435Notes

Reaction equation

HRID 2293435 reaction equation
C([Li])CCC.C[Si](C)(C)[CH:8]1[S:13][CH2:12][CH2:11][CH2:10][S:9]1.[N:16]12[CH2:24][CH:20]([C:21](=O)[CH2:22]1)[CH2:19][CH2:18][CH2:17]2.O>CCCCCC.C1COCC1>[S:9]1[CH2:10][CH2:11][CH2:12][S:13][C:8]1=[C:21]1[CH2:22][N:16]2[CH2:24][CH:20]1[CH2:19][CH2:18][CH2:17]2

Participants

7

Reactant 4

HCID 962WaterHCID 834132-Trimethylsilyl-1,3-dithianeHCID 4183471-azabicyclo[3.2.1]octan-6-oneHCID 178418339Butyllithium

Product 1

HCID 21476660HCID 21476660, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

n-Butyl lithium (6.05 ml of a 1.6M solution in hexane, 9.7 mmol) was added dropwise to a solution of 2-trimethylsilyl-1,3-dithiane (1.86 g, 9.7 mmol), in THF (30 ml) at -30° C. and the reaction mixture stirred for 2 hr. A solution of 1-azabicyclo [3.2.1]octan-6-one (1.1 g, 8.8 mmol) in THF (10 ml) was added dropwise and the reaction mixture allowed to warm to room temperature. Water (20 ml) was added and extracted (3×50 ml) with dichloromethane. The combined extracts were dried (MgSO4) and evaporated and the residue chromatographed through alumina eluting with dichloromethane/methanol (97:3) to afford the title compound as a clear liquid, (2 g), m/e 227 (M+); δ(60 MHz; CDCl3) 1.10-2.90 (15H, m, 7×CH2 and CH); 3.38 (2H, AB q, J=17 Hz, CH2 --C=C).

Workup

  1. extractionextracted (3×50 ml) with dichloromethane
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customevaporated
  4. customthe residue chromatographed through alumina eluting with dichloromethane/methanol (97:3)

Sources & evidence

ORD record
ord-50534a02813c4668957243337b951bf6
Source dataset
uspto-grants-1997_11
Patent number
US05686463

Reaction notes

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