Hydrochloric Acid → 1638651-87-2

HRID 1778504Notes

Reaction equation

HRID 1778504 reaction equation
CC(=CC)C.[CH:6]([C:8]12[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:12]([CH2:13][CH2:14]1)[CH2:11][O:10][CH2:9]2)=[O:7].CC(=CC)C.C1C[O:31]CC1.[O-]Cl=O.[Na+].Cl>O.C(O)(C)(C)C.C1COCC1>[C:19]([O:18][C:16]([N:15]1[C:8]2([C:6]([OH:31])=[O:7])[CH2:14][CH2:13][CH:12]1[CH2:11][O:10][CH2:9]2)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 117698030HCID 117698030, compoundHCID 131734820HCID 131734820, compound

Product 1

HCID 1176981981638651-87-2Yield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 50 ml of flask fitted with magnetic stirrer was charged with 5 ml of THF and was cooled to −78° C., to which 2-methyl-2-butene (0.15 mL, 3 mmol) was added and stirred for 5 minutes. Another 50 ml of flask fitted with magnetic stirrer was charged with tert-butyl 5-formyl-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate (71 mg, 0.3 mmol) and tert butanol (5 mL) and was stirred at 25° C., to which the above prepared 2-methyl-2-butene THF solution was added. The resulting mixture was cooled to 0° C., and then a solution of NaH2PO4 (81 mg, 0.52 mmol) in water (5 mL) and a solution of NaClO2 (20 mg, 0.22 mmol) in water (5 mL) were added subsequently. After stirring for 20 minutes at 0° C., the reaction mixture was diluted with water (10 mL), acidified to pH 5-6 using 1N HCl, and extracted with ethyl acetate (50 mL) three times. The combined organic phases were dried over Na2SO4, and concentrated in vacuo to afford 8-tert-butoxycarbonyl-3-oxa-8-azabicyclo[3.2.1]octane-5-carboxylic acid 81k (40 mg, 51%), which was used for next step without further purification. MS: calc'd (MH+) 258, measured (MH+) 258

Workup

  1. customA 50 ml of flask fitted with magnetic stirrer
  2. additionwas added
  3. customAnother 50 ml of flask fitted with magnetic stirrer
  4. stirringwas stirred at 25° C., to which the
  5. additionwas added
  6. stirringAfter stirring for 20 minutes at 0° C.
  7. extractionextracted with ethyl acetate (50 mL) three times
  8. dry with materialThe combined organic phases were dried over Na2SO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5973839de77403aaebfdb056a8240cc
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

Loading…