Acetic Acid → HCID 46213239, compound

HRID 1092551Notes

Reaction equation

HRID 1092551 reaction equation
C[CH:2](C)[CH:3](C1C=CC=CC=1)[C:4]([NH:6][C@@H:7]1[C@H:14]2[C@H:10]([CH2:11][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[CH2:13]2)[CH2:9][CH2:8]1)=O.C(O[C:36]1(O[Si](C)(C)C)[CH2:38][CH2:37]1)C.C(O)(=O)C.C([BH3-])#N>ClCCl>[CH:4]1([N:6]([CH:36]2[CH2:37][CH2:38]2)[C@@H:7]2[C@H:14]3[C@H:10]([CH2:11][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=4)[CH2:13]3)[CH2:9][CH2:8]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 498716Cyano-borohydrideHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 665909373-methyl-2-phenyl-N-{(3aS*,4S*,6aR*)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}butanamide

Product 1

HCID 46213239HCID 46213239, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3aS*,4S*,6aR*)-2-(3-(Trifluoromethyl)benzyl)octahydrocyclopenta[c]pyrrol-4-amine (228 mg, 0.802 mmol) from Example 122 Step E and (1-ethoxycyclopropoxy)trimethylsilane (140 mg, 0.802 mmol) were combined in dichloromethane (1.5 mL) and 5 mL of acetic acid was added. The reaction was stirred at room temperature for 20 minutes, and then PS-cyanoborohydride (343 mg, 0.802 mmol) was added. The reaction was heated to 40° C. overnight. Silica gel chromatography eluting with 1-10% methanol (2 N ammonia)/dichloromethane to gave the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 7.58 (s, 1H), 7.48 (d, J=7.6, 2H), 7.42 (d, J=7.6, 1H), 3.64 (d, J=13.6, 1H), 3.51 (d, J=13.6, 1H), 2.94-2.82 (m, 3H), 2.80-2.71 (m, 2H), 2.55 (dd, J=5.4, 9.4, 3H), 2.41 (t, J=8.3, 1H), 2.16 (dd, J=4.7, 8.7, 1H), 1.97-1.70 (m, 7H), 1.70-1.59 (m, 3H), 1.40 (dd, J=6.7, 12.6, 1H); MS (ESI+) m/z 365 (M+H)+.

Workup

  1. temperatureThe reaction was heated to 40° C. overnight
  2. washSilica gel chromatography eluting with 1-10% methanol (2 N ammonia)/dichloromethane

Sources & evidence

ORD record
ord-c39dc8b2fdfc4aabbed13ee24e1521b0
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

Loading…