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

HRID 1407673Notes

Reaction equation

HRID 1407673 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″(1′H)-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-ebf5e45b3708412391b6c8c96aba27d1
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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