Acetone → HCID 46888080, compound

HRID 882770Notes

Reaction equation

HRID 882770 reaction equation
[N:1]1([C:8]([C@H:10]2[CH2:14][C@H:13]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH2:12][N:11]2[C:23](=[O:25])[CH3:24])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:26][C:27]([CH3:29])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:15][C@@H:13]1[CH2:12][N:11]([C:23](=[O:25])[CH3:24])[C@@H:10]([C:8]([N:1]2[CH2:7][CH2:6][CH2:5][N:4]([CH:27]([CH3:29])[CH3:26])[CH2:3][CH2:2]2)=[O:9])[CH2:14]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 44599397HCID 44599397, compound

Product 1

HCID 46888080HCID 46888080, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (2R,4S)-1-[2-([1,4]diazepane-1-carbonyl)-4-(3-fluoro-phenoxy)-pyrrolidin-1-yl]-ethanone (220 mg, 0.63 mmol) in dichloroethane (3 mL) was added acetone (324 μL, 4.41 mmol) and sodium triacetoxyborohydride (199 mg, 0.945 mmol). After 2 days, the reaction mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2 (4×). The combined organic layers were dried and concentrated. Purification of the residue by FCC provided the desired product (205 mg, 83%). MS (ESI): mass calcd. for C21H30FN3O3, 391.23; m/z found, 392.3 [M+H]+. 1H NMR (CDCl3): 7.22 (ddd, J=8.3, 8.3, 6.9 Hz, 1H), 6.69-6.64 (m, 1H), 6.63 (dd, J=8.3, 2.3 Hz, 1H), 6.57 (ddd, J=10.6, 2.2, 2.2 Hz, 1H), 5.09-5.03 (m, 1H), 5.00-4.95 (m, 1H), 4.03 (dd, J=11.1, 4.9 Hz, 1H), 3.74-3.59 (m, 4H), 3.55-3.45 (m, 1H), 2.92-2.78 (m, 1H), 2.75-2.51 (m, 4H), 2.40-2.23 (m, 2H), 2.04 (s, 3H), 2.01-1.92 (m, 1H), 1.85-1.67 (m, 1H), 1.00-0.94 (m, 6H).

Workup

  1. additionthe reaction mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2 (4×)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customPurification of the residue by FCC

Sources & evidence

ORD record
ord-c99f17c5bb8c4b068912585de1ff09c7
Source dataset
uspto-grants-2012_08
Patent number
US08236792B2

Reaction notes

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