Acetic Acid → HCID 117601123, compound

HRID 578952Notes

Reaction equation

HRID 578952 reaction equation
[F:1][C:2]1([F:16])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:5][NH:4][CH2:3]1.[C:17]([BH3-])#N.[Na+].C=O.C(O)(=O)C>C1COCC1.C(OCC)(=O)C.CO>[F:16][C:2]1([F:1])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:6][CH2:5][N:4]([CH3:17])[CH2:3]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 56924440tert-Butyl 6,6-difluoro-1,4-diazepane-1-carboxylate

Product 1

HCID 117601123HCID 117601123, compoundYield 98.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Combined tert-butyl 6,6-difluoro-1,4-diazepane-1-carboxylate (49 mg, 0.207 mmol) and sodium cyanoborohydride (52 mg, 0.83 mmol) in THF (1.5 mL) and added 37% aqueous formaldehyde (0.077 mL, 1.037 mmol) and acetic acid (0.018 mL, 0.311 mmol) and then stirred at 20° C. for 16 h. Then methanol (300 uL) was added and the mixture was concentrated in vacuo to give a residue which was taken up in ethyl acetate (40 mL), washed with saturated aqueous sodium bicarbonate (50 mL) and brine, dried with magnesium sulfate and concentrated in vacuo to give the title compound (51 mg, 0.204 mmol, 98%) as a clear, colorless oil. MS: 251 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.46 (s, 9 H) 2.50 (s, 3 H) 2.73 (d, J=4.8 Hz, 2 H) 2.92 (t, J=13.5 Hz, 2 H) 3.55 (d, J=4.8 Hz, 2 H) 3.75-3.94 (m, 2 H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a residue which
  3. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21de13718b3c4e13a831828d94616203
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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