Tetrahydrofuran → tert-butyl (1S,2S,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

HRID 1662093Notes

Reaction equation

HRID 1662093 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH:14]=[CH:13][C:12](=O)[N:11]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:23]1COCC1>C(OCC)C>[Si:1]([O:8][CH2:9][C@H:10]1[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@H:13]2[C@@H:14]1[CH2:23]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 108711501,1-Dimethylethyl (2S)-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2,5-dihydro-5-oxo-1H-pyrrole-1-carboxylate

Product 1

HCID 59369795tert-butyl (1S,2S,5R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 4-3 (0.25 g, 0.76 mmol) in diethyl ether (3.8 mL) at 0° C. was added a solution of CH2N2 (7.6 mmol, made from treatment of 1-methyl-3-nitro-1-nitrosoguanidine with 40% KOH) in diethyl ether (5 mL) under nitrogen and the reaction mixture was stirred 2 h. The reaction was dried over magnesium sulfate and concentrated directly to yield an oil of >90% purity. The product was used without further purification. The oil was resuspended in THF (1.7 mL) at ambient temperature and to the mixture was added borane-tetrahydrofuran complex in THF (2.4 mL, 2.4 mmol, 1.0M solution). The reaction was stirred 15 h and quenched with methanol (2 mL). The combined organic phase was dried over magnesium sulfate and concentrated. The residue was purified by normal phase silica gel chromatography (0 to 65% EtOAc in hexanes) to afford the product (4-4) as an oil.

Workup

  1. dry with materialThe reaction was dried over magnesium sulfate
  2. concentrationconcentrated directly
  3. customto yield an oil of >90% purity
  4. customThe product was used without further purification
  5. customwas resuspended in THF (1.7 mL) at ambient temperature and to the mixture
  6. stirringThe reaction was stirred 15 h
  7. customquenched with methanol (2 mL)
  8. dry with materialThe combined organic phase was dried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by normal phase silica gel chromatography (0 to 65% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1ef10e49da704a8fb2d68d1cdd5fc933
Source dataset
uspto-grants-2011_10
Patent number
US08030495B2

Reaction notes

Loading…