9-Borabicyclo(3.3.1)nonane → HCID 59226062, compound

HRID 2370283Notes

Reaction equation

C([O:5]C(=O)NC1(CCCO)CCC(OC2C=C3C(=CC=2Cl)C(OCC2C=CC=CC=2)=NC=C3)CC1)(C)(C)C.[C:39]([O:43][C:44](=[O:77])[NH:45][C:46]1([CH2:74][CH:75]=[CH2:76])[CH2:53][CH2:52][CH2:51][CH:50]([O:54][C:55]2[CH:56]=[C:57]3[C:62](=[CH:63][C:64]=2[Cl:65])[C:61]([O:66][CH2:67][C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)=[N:60][CH:59]=[CH:58]3)[CH2:49][CH2:48][CH2:47]1)([CH3:42])([CH3:41])[CH3:40].B1C2CCCC1CCC2>>[C:39]([O:43][C:44](=[O:77])[NH:45][C:46]1([CH2:74][CH2:75][CH2:76][OH:5])[CH2:53][CH2:52][CH2:51][CH:50]([O:54][C:55]2[CH:56]=[C:57]3[C:62](=[CH:63][C:64]=2[Cl:65])[C:61]([O:66][CH2:67][C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)=[N:60][CH:59]=[CH:58]3)[CH2:49][CH2:48][CH2:47]1)([CH3:42])([CH3:41])[CH3:40]

Participants

Reactant 3

HCID 789669-Borabicyclo(3.3.1)nonane

HCID 59226061HCID 59226061, compound

HCID 59226073HCID 59226073, compound

Product 1

HCID 59226062HCID 59226062, compound

Procedure

1.14 g of [5-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-1-(3-hydroxy-propyl)-cyclooctyl]-carbamic acid tert-butyl ester (59) were synthesized using the procedure described for the synthesis of [4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-1-(3-hydroxy-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (53) starting from 1.17 g (2.12 mmol) of [1-allyl-5-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclooctyl]-carbamic acid tert-butyl ester (58) and 12.7 mL (6.37 mmol) of 9-BBN (0.5M solution in THF). Rt=1.71 min (Method I). Detected mass: 569.3 (M+H+).

Sources & evidence

ORD record: ord-7085020508fe4b098f7a3d202954839b
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710077B2

Reaction notes

Loading…