Triethylamine → HCID 10105889, compound

HRID 744134Notes

Reaction equation

HRID 744134 reaction equation
C(OC(N1CCC[C@H]1C([N:18]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1)=O)=O)C1C=CC=CC=1.[CH2:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])C.[C:36](OCC)(=O)C>>[CH3:28][O:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[NH:18][CH:19]=[C:20]2[CH2:33][C@@H:32]1[CH2:36][CH2:35][CH2:34][N:31]1[CH3:29]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 53836934HCID 53836934, compound

Product 1

HCID 10105889HCID 10105889, compoundYield 22%

Procedure

(S)-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-methoxy-1H-indole was used. The chromatographic eluent was 8% triethylamine in ethyl acetate to afford the title compound (yields ranged from 22 to 57%) as an oil: IR (CHCl3) 3475, 1625, 1585, 1480, 1455 cm-1 ; 1H NMR (CDCl3) δ8.13 (br s, 1H), 7.23 (d, J=8.8 Hz, 1H), 7.04 (d, J=2.4 Hz, 1H), 6.97 (d, J=2.2 Hz, 1H), 6.84 (dd, J=2.4 and 8.8 Hz, 1H), 3.86 (s, 3H), 3.17-3.10 (m, 2H), 2.58 (dd, J=9.9 and 13.9 Hz, 1H), 2.50-2.40 (m, 1H), 2.47 (s, 3H), 2.26-2.17 (m, 1H), 1.89-1.72 (m, 2H), 1.70-1.52 (m, 2H); 13C NMR (CDCl3) δ153.8, 131.4, 128.2, 122.7, 113.9, 111.8, 111.7, 101.1, 66.6, 57.5, 56.0, 40.8, 31.5, 30.0, 21.9; LRMS, m/z (relative intensity) 244 (M+, 7), 160 (20), 145 (16), 117 (21), 84 (100); HRMS: calculated for C15H20N2O: 244.1573; found: 244.1575; [α]25D =-96° (CHCL3, c=1.0).

Sources & evidence

ORD record
ord-04f55bdd2a1f4253a7aafbeeb43f32b1
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

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