Water → HCID 21476660, compound

HRID 1654103Notes

Reaction equation

HRID 1654103 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.O1CCCC1>[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 tetrahydrofuran (30 ml) at -30° C. and the reaction mixture stirred for 2 hours. A solution of 1-azabicyclo[3.2.1]octan-6-one (1.1 g, 8.8 mmol) in tetrahydrofuran (10 ml) was added dropwise and the reaction mixture allowed to warm to room temperature. Water (20 ml) was added and extracted (3×) with dichloromethane. The combined extracts were dried (MgSO4) and concentrated and the residue purified by chromatography on alumina eluting with dichloromethane/methanol (97:3) to give the title compound as a colourless oil (2 g); m/e 227 (M+); δ (360 MHz, CDCl3) 1.23-1.38 and 1.56-1.86 (1H and 3H respectively, each m, 3CH2 and 4CH2 ), 2.08-2.24 (2H, m, SCH2CH2), 2.76-3.00 (9H, m, 2×SCH2, 2CH2, 5CH and 8CH2), 3.42 (1H, d, J=17 Hz, one of 7CH2) and 3.56 (1H, d, J=17 Hz, one of 7CH2).

Workup

  1. extractionextracted (3×) with dichloromethane
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. customthe residue purified by chromatography on alumina eluting with dichloromethane/methanol (97:3)

Sources & evidence

ORD record
ord-c8bbe535fc3c4cc08da7abbd43d35ad4
Source dataset
uspto-grants-1995_04
Patent number
US05405853

Reaction notes

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