Sodium Chloride → tert-butyl N-[4-(hydroxymethyl)oxan-4-yl]carbamate

HRID 1968874Notes

Reaction equation

HRID 1968874 reaction equation
CN1CCOCC1.[C:8]([O:12][C:13]([NH:15][C:16]1([C:22](O)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].ClC(OCC(C)C)=O.[BH4-].[Na+].[Cl-].[Na+]>O1CCCC1.CO>[C:8]([O:12][C:13](=[O:14])[NH:15][C:16]1([CH2:22][OH:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)([CH3:11])([CH3:9])[CH3:10]

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 12682194-(Boc-amino)tetrahydropyran-4-carboxylic acidHCID 4311764Sodium borohydride

Product 1

HCID 67114425tert-butyl N-[4-(hydroxymethyl)oxan-4-yl]carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Neat 4-methylmorpholine (2.7 mL, 24.6 mmol) was added, via syringe, to a rapidly stirred, 0° C., solution of 4-tert-butoxycarbonylamino-tetrahydro-pyran-4-carboxylic acid (5.0 g, 20.4 mmol) and isobutyl chloroformate (3.2 mL, 24.5 mmol) in anhydrous tetrahydrofuran (200 mL) contained in a 1000 mL round bottomed flask. Precipitate immediately formed. The suspension was allowed to stir at 0° C. under N2 blanket for 20 minutes then a hand swirled, gas evolving, suspension of sodium borohydride (2.3 g, 61.3 mmol) in methanol (65 mL) was added, at as fast of a rate as possible while maintaining control of the concomitant reaction foaming. When observable gas evolution had ceased the opaque white reaction suspension was transferred to a separatory funnel containing saturated aqueous sodium chloride (500 mL) and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4), passed through a plug of silica gel, and evaporated to obtain 4.89 g of off white solid which was used without further purification. LRMS (ESI) m/z 232.2 [(M+H)+, calcd for C11H22NO4232.3].

Workup

  1. customPrecipitate immediately formed
  2. stirringto stir at 0° C. under N2 blanket for 20 minutes
  3. additionwas added
  4. temperatureat as fast of a rate as possible while maintaining control of the concomitant reaction foaming
  5. customwas transferred to a separatory funnel
  6. extractionextracted with ethyl acetate
  7. dry with materialCombined organic extracts were dried (MgSO4)
  8. customevaporated
  9. customto obtain 4.89 g of off white solid which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-f3ed0eba1def47d18f7b64cfec9629eb
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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