4-Benzyloxybenzyl chloride → HCID 59352143, compound

HRID 1965651Notes

Reaction equation

HRID 1965651 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@:3]2([C:21]3[C:12](=[CH:13][C:14]4[O:19][CH2:18][CH2:17][O:16][C:15]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=[O:22].C[C:24]1[C:28]2[CH:29]=[C:30]3[C:35]4([C:43]5[C:38](=[CH:39][CH:40]=[CH:41]C=5)NC4=O)[CH2:34][O:33][C:31]3=[CH:32][C:27]=2ON=1.C(OC1C=CC(CCl)=CC=1)C1C=CC=CC=1.BrCC1OC(C(F)(F)F)=CC=1>>[CH2:34]([O:33][C:31]1[CH:32]=[CH:27][C:28]([CH2:24][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C@@:3]3([C:21]4[C:12](=[CH:13][C:14]5[O:19][CH2:18][CH2:17][O:16][C:15]=5[CH:20]=4)[O:11][CH2:10]3)[C:2]2=[O:22])=[CH:29][CH:30]=1)[C:35]1[CH:43]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 4

HCID 700424-Benzyloxybenzyl chlorideHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 59352191Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydro-, (3'S)-HCID 593524533-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3'-indol]-2'(1H)-one

Product 1

HCID 59352143HCID 59352143, compound

Procedure

Following the procedure described in EXAMPLE 9 and making non-critical variations using (8S)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1H)-one, and 4-benzyloxybenzyl chloride to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, (8S)-1′-[4-(benzyloxy)benzyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (95%) as a colorless solid: mp 151-153° C.; 1H NMR (300 MHz, DMSO-d6) δ7.45-7.23 (m, 8H), 7.18-7.14 (m, 1H), 7.05-6.97 (m, 4H), 6.53 (s, 1H), 6.06 (s, 1H), 5.07 (s, 2H), 4.86 (ABq, J=27.9, 15.6 Hz, 2H), 4.73 (ABq, J=39.9, 9.3 Hz, 2H), 4.22-4.07 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 176.6, 157.7, 154.6, 144.1, 142.1, 137.8, 136.9, 131.7, 128.7, 128.6, 128.4, 128.3, 127.8, 127.6, 123.5, 122.9, 121.2, 114.9, 110.8, 109.4, 98.8, 79.4, 69.1, 64.1, 63.5, 57.2, 42.4; MS (ES+) m/z 491.8 (M+1).

Sources & evidence

ORD record
ord-f404b7de4abb4277b5f27d3ce6299296
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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