2-(Bromomethyl)tetrahydro-2H-pyran → HCID 59352194, compound

HRID 1965526Notes

Reaction equation

HRID 1965526 reaction equation
BrC[C@@H:3]1[CH2:7][CH2:6][NH:5][C:4]1=[O:8].Br[CH2:10]C1CCCCO1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]2([C:29]3=[CH:30][C:31]4[O:35][CH2:34][O:33][C:32]=4[CH:36]=[C:28]3[O:27][CH2:26]2)[C:18]1=[O:37]>>[O:8]=[C:4]1[NH:5][C@H:6]([CH2:10][N:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3([C:29]4=[CH:30][C:31]5[O:35][CH2:34][O:33][C:32]=5[CH:36]=[C:28]4[O:27][CH2:26]3)[C:18]2=[O:37])[CH2:7][CH2:3]1

Participants

4

Reactant 3

HCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 68599093HCID 68599093, compound

Product 1

HCID 59352194HCID 59352194, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using (R)-3-bromomethyl-2-pyrrolidinone to replace 2-(bromomethyl)tetrahydro-2H-pyran, and spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1H)-one, 1′-{[(2S)-5-oxopyrrolidin-2-yl]methyl}spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one was obtained (47%) as a colorless solid: mp 121-130° C.; 1H NMR (300 MHz, CD3OD) δ7.34 (dd, J=7.6, 7.6 Hz, 1H), 7.22-7.06 (m, 4H), 6.48 (d, J=1.9 Hz, 1H), 6.15 (d, J=9.3 Hz, 1H), 5.82 (d, J=1.4 Hz, 2H), 4.86-4.81 (m, 2H), 4.64 (dd, J=9.3, 3.8 Hz, 1H), 4.13-4.06 (m, 1H), 3.85-3.83 (m, 2H), 2.43-2.18 (m, 2H), 2.00-1.88 (m, 1H); 13C NMR (75 MHz, CD3OD) δ177.9, 177.4, 177.3, 154.7, 154.6, 147.5, 147.4, 141.2, 140.8, 140.8 136.0, 130.8, 130.6, 127.3 127.2, 127.0, 126.3, 123.4, 122.0, 121.9, 121.9 118.0, 117.8, 107.4, 101.1, 100.0, 99.9, 91.3, 91.3, 78.8, 78.7, 56.8 (2C), 51.4, 51.2, 43.2 (2C), 27.6, 22.6, 18.6; MS (ES+) m/z 401.2 (M+23), 379.2 (M+1).

Sources & evidence

ORD record
ord-800bb3cda4044be3baa80036d477ad51
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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